41 isn't so big until something is going wrong - which will, and often, when sailing with as much experience as this original poster has.

Bigger boats are slow ... I think the person who suggested that is a troll ... Bigger boats are slower in the same way riding up in an SUV feels slower than down in an MG; perspective is everything.

The flip side of Bigger/Slower is Size = Inertia. The posts about "docking" allude to this, but nobody is stating it ... that 40+ sailboat may be moving "slowly"; when it hits the dock, the dock will be moving "slowly" as well.

Anyway, I enjoyed learning to sail in small boats ( I even lived on some, sometimes ) and also enjoyed sailing larger sailboats ( I even lived on some, longer times ). The respective skills are complementary not exclusive.

Reading the original post, I get the sense there is more of a desire to BUY something, than to USE something.

We learned to sail on a 43ft boat. We live in it during the summers and sail as much as we can. It can definetly be done. We hired 2 captains for a week. One whose primary job was sailing the boat through the East coast, the other whose job was teaching me and my wife. Maybe unorthodox but it worked. We also did the ASA courses and would make that a must do. I'm not claiming that taught us anywhere close to everything we needed to know. Just enough to be safe. In 7 years of living/sailing we've definetly learned much more.

With that said. If I were you I would make a bow thruster a must have, it will be invaluable with your current skill level.

Yes, the right 40-43 ft boat can be singlehanded easily, ours can. I second all the coments that the hard part will be docking wihout an extra pair of hands. I recommend a new girlfriend to help with that part.

BTW if you're interested our 43 ft boat is going up for sale (5'2" draft). We're upgrading to a 50 ft boat. And no I wouldn't suggest starting with a 50-60 ft boat. 40-43 ft max.

if you do buy a big new boat get some lessons in a rental - ding the dock with someone else's boat first...

I doubt the charter company will let you take their boat out without experience. It you ding their boat, expect to pay a high cost plus markup.

Go take lessons and sign on as a crew to learn the ropes, there is no short cut in life, but smart person will learn faster than others. Since the OP is independently wealthy, I assume he makes his fortunate by himself, so I assume he is a sharp person, so sailing would be an easy task to learn.
I am sure he will be fine whatever he chooses.

Jumping headlong into a "Big Boat" without the years of experience that it takes to become a "Sailor" is not at all recommended.

Then I'd advise the guy to definitely not become a "Sailor" (whatever it means within these highfalutin quotes). I know many people who jumped "headlong into a 'Big Boat'" without a lick of experience. Amazingly, they're still living to talk about it.

There's a variety of ways to gain experience safely after buying your boat, many of which have been suggested here. I agree that a tight slip in a marina might be a deterrent to sail at first, so choose your boat's home accordingly. If you can get by on a mooring, you'll probably sail the boat a whole lot more, but many can't get by without the comforts of being dockside.

With more and more people seemingly have a fair amount of money to spend, 'jumping into a big boat' does seem to be becoming the norm these days. And of course it's do-able. Where 20-25 footers used to be your typical 'starter', that's certainly moved up into the 30s and higher.

Sometimes it's hard to give up on the 'traditional ways'...and to me it still seems a logical progression to start/learn on the smaller side of the scale and move your way up as your skill and comfort levels grow... but EMMV...

You guys/gals saying it is easy to single hand dock a 40 foot or larger boat in an unfamilar (or even a familar) marina are blowing a lot of smoke. Maybe that is the case if there is no wind or current, but if there is, things get very difficult. Maybe the Hunter joy stick control will make things easy (by using both a prop thruster and sail drive)- but not all boats have that, but maybe that is what the OP needs to have- but what do you do not "if" but "when" it breaks.

I single my 34 quite a bit, and docking is never easy and it is always stressful. Normally I am dealing with quite a bit of wind and current. The problem is once things start to go wrong, it is very hard to recovery when you are alone. If I could only push my bow off with 10 lbs of force I would be good. But how do I get to the bow when I need to be at the tiller? Sure you can rig lines to help the single hander, but things still go wrong. And this is not just me becasue of my lack of years and years of experience. I have seen very experienced sailing instructors have difficulty docking a 40 footer with two on board, and an ex sea captain hitting the dock, even with years of docking experience. With wind and current, docking is always hard- that is why the big boys have tugs. Sometimes the best you can do is if you are going to collide with somthing, try to do it lightly and damage only your own boat, if anything.

I would think sailing to the Bahamas alone on would not be the most relaxing thing to do. Having to steer, navigate, tend to the boat, sleep all alone would be stressful as would bringing the boat into an unfamilar harbor.

Definietly get out and try chartering in Bahamas or Carribean and get the feel of a big boat, and what it is really like out there, and take some friends with you.

What's your real goal? Is it to live on the water, or to save money? Both were in the beginning of your original post. If you want a boat that you can live on and still handle singlehanded as a novice sailor, I'd suggest looking at something in the 25-35' range, and probably more in the 27-30. These aren't great as floating condos, but if you pick up a used one for $20-30K, you'll be able to find something that's decent and disposable given your budget (or lack thereof). Live on it for a year, see what you like/don't like, and hone your skills. Then move up to a 40-something if/when you think you're ready for it.

Most of the folks I know or have known to live on boats, never sail the boat, or at least sail very rarely. Just takes to much time to pack and prep all the accumulated junk to get ready to go to sea. Add that to a boat that is near your range of size to handle, and you will always tend to talk yourself out of going sailing. Might be better to find a condo/apartment on the water next to your docked boat- best of both worlds.

Hi everyone, I'm overwhelmed by all the great advice and words of caution. I had to look up what a bow thruster was (still don't quite get it, but seems to be a prop in the front to help make turns) and other advice you have all given, and it has only shown that I don't know what I don't know.

My logic has been thus. Just got divorced and lost my house, dog, etc (losing the dog really hurts). Since it's just me, I can now live anywhere in the world, even a tent if i had to, while I get my life back together. I need a short term plan until I figure out my long term plan. I could move back to NYC where my life would revolve around bars and restaurants, traffic on weekends if I wanted to get away, with a boat somewhere. Hate the weather and lifestyle, can only sail in summer, and having been there 10 years, want something new. Second choice was California, maybe SD of SF, with SF seeming like a better choice given the sailing, weekend trips in the mountains, access to Vegas, and city itself. Weather isn't so great, but better lifestyle and access to women in the city. This is probably where I'll end up, but the water is cold and can't jump off boat. So finally, I figured i could move to Miami and live on South Beach near warm water, sail year round, enjoy weather and access to women, plus use weekends sailing to vacation-like places with access to longer vacations to Bahamas and Caribbean, it was a great short term plan until I know what the heck to do. Looking at apartments on South Beach, many were small, and living in a larger apartment alone didn't seem like a good choice day 1. So then if I moved into a tiny apt and bought a boat, the boats I looked at were NICER, although maybe not as big, but close enough in comparison to a small apartment / townhouse on the beach.

So my logic was why not try to live in a bigger boat, but one that wasn't so big that I couldn't use it, but big enough to sail on and leverage on weekends or week trips until I figure out my long term plan. hen I could sial it to SF or NYC or whatever I end up doing and have it as my weekend/summer toy. But in the meantime, learn how to use it in Miami and enjoy life a bit. That's the genesis behind my question.

If I just lived on board and never took it out, my friend said I'd still have to get it up river in Miami during hurricanes, so no matter what, iI'm going to have to know how to sail it. And If i live on a boat up river, not sure if that's on a mooring or in a marina, so I need to look into that. If this dream is impossible, then i can get a starter boat and live in a condo, but seems like some people think its' ok and others think I'm going to get into trouble.

I did go to the Spring Sailboat Annapolis show earlier this month just to see what was livable. Then I mashed up minimum size I could live on with smallest keel size so I could use it down Florida, and came to same conclusion many have come up with - catamaran is most logical choice, but most of the room is spent on beds and I'm alone, it's a waste of space. That is still an option since those can sail into skinny water, but wasn't sure for a single guy if wanted it. I do like the nets in front and think chicks would like to lounge on that as opposed to the small back of a sailboat, so its still an option. With that said, I then looked at the Hunter since it had the best inside look and space, plus the 'master bedroom,' along with smallest keel size (Island Packet had even smaller keel size, but I didn't love the interior).

Why I don't pick a different boat or more upscale boat are good questions, and I could, but just wanted to balance cool interior with functionality. The Halberg looked nice, but didn't have a master bedroom that I could live on. I also need to research what the buttons on the winch mean in terms of 1 finger sailing to see if that's a good tradeoff or not. Finally, I'm not living on any boat unless I can get DirectTV (I see its available on boats) so i can watch my football on Sundays.

With that said, love the advice and hope it keeps coming. Seems if I can learn to dock, i'm in business. Being a passenger on a boat, I assume the only reason I can't dock solo is that I want someone to jump off and put the rope on the hooks and help pull boat in, correct? That's something I can't do alone unless I pull it in perfectly and cut off engine at right time, coast in, etc?

Because I don't know what I don't know yet, it seems like the advice given is that sailing solo is much easier, except when I get into trouble. Then it's life or death. When in trouble, which I assume is too much wind, can't i just drop sails and batten down the hatches? I've read in horrible situations, sailors would cut off sails if need be, and be three sheets to the wind. As a newbie have always wanted to ask that.

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